Synthesis, radical scavenging activity and structure–activity relationship of uric acid analogs

MedChemComm ◽  
2013 ◽  
Vol 4 (3) ◽  
pp. 527 ◽  
Author(s):  
Daisuke Yasuda ◽  
Kyoko Takahashi ◽  
Tomohiro Kakinoki ◽  
Yoko Tanaka ◽  
Tomoyuki Ohe ◽  
...  
2017 ◽  
Vol 12 (12) ◽  
pp. 1934578X1701201
Author(s):  
Natalia K. Utkina ◽  
Natalia D. Pokhilo

The ABTS•+ radical cation scavenging activity of known (2-5, 9, 10) and new (6-8) 1’-hydroxyethylnaphthazarins and their products of esterification and etherification was evaluated and a structure-activity relationship was studied. It was shown, that the structure of side chains does not affect the radical scavenging activity of 1’-hydroxyethylnaphthazarins and their derivatives. The presence of methoxyl groups on the naphthazarin core slightly enhanced the antioxidant activity of compounds compared with compounds without methoxyl groups. The presence of the additional hydroxyl group on the naphthazarin moiety of isonorlomazarin (5) and its derivative (6) is essential for the activity.


2007 ◽  
Vol 10 (4) ◽  
pp. 537 ◽  
Author(s):  
Ju-Mi Jeong ◽  
Cheol-Hee Choi ◽  
Su-Kyeong Kang ◽  
In-Hwa Lee ◽  
Ji-Yoon Lee ◽  
...  

Purpose. Flavonoids have been used as antioxidant, chemopreventive and chemosensitizing agents. In this study, eleven flavonoids containing a variety of hydroxy (OH) and/or methoxy (OMe) groups were evaluated for their antioxidant, cytotoxic and chemosensitizing effects to create a structure-activity relationship (SAR). Methods. 1,1-Diphenyl-2-picrylhydrazyl (DPPH) radical solution-based chemical assay and and 2',7'-dichlorofluorescin diacetate (DCFH-DA) cellular-based assay were used to compare the free radical scavenging activity on the same molar concentration basis using the AML-2/DX100 cells which are characterized by the down-regulated expression of catalase and resulting supersensitiviy to hydrogen peroxide. The chemosensitization and cytotoxicity were determined by the MTT assay in the presence or absence of an anticancer drug using the P-glycoprotein-overexpressing AML-2 subline AML-2/D100 cells. Results. The antioxidant activity of the flavonoid (3,5,7,3’,4’-OH) was higher than that of the flavonoid (5,7,3’,4’-OH). Flavonoids substituted with the various number of OMe decreased antioxidant activity. Flavonoids with 7-OH or 5,7-OH groups have the highest cytotoxicity, and flavonoids with 5,7-OMe group intermediate cytotoxicity. The IC50 values of flavonoid (5,7-OMe, 3’,4’,5’-OMe) and flavonoid (5,7-OMe, 4’-OMe), 0.4 M and 1.4 M. The IC50 values of flavonoid (5,6,7-OMe, 3’,4’-OMe) and flavonoid (5,6,7-OMe, 3’,4’,5’-OMe), 3.2 uM and 0.9 M, respectively, and those of flavonoid (5,6,7-OMe, 3’,4’,5’-OMe) and flavonoid (5,7-OMe,3’,4’,5’-OMe) were 0.9 M and 0.4 M, respectively. Conclusions. These results suggest that flavonoids with 3-OH group play a positive role in antioxidant activities, flavonoids with 5-OH and/or 7-OH groups show the higher cytotoxicity, and flavonoids with 3’-OMe and/or 5’-OMe groups plays positive but 6-OMe groups negative roles in the P-glycoprotein (Pgp) inhibition. It is believed that these SAR results can be taken into account for the development of flavonoids with high therapeutic index.


1995 ◽  
Vol 47 (1-3) ◽  
pp. 327-331 ◽  
Author(s):  
J. P. Hu ◽  
M. Calomme ◽  
A. Lasure ◽  
T. De Bruyne ◽  
L. Pieters ◽  
...  

MedChemComm ◽  
2016 ◽  
Vol 7 (11) ◽  
pp. 2193-2193
Author(s):  
Wenzhen Liao ◽  
Longjian Gu ◽  
Yamei Zheng ◽  
Zisheng Zhu ◽  
Mouming Zhao ◽  
...  

Correction for ‘Analysis of the quantitative structure–activity relationship of glutathione-derived peptides based on different free radical scavenging systems’ by Wenzhen Liao et al., Med. Chem. Commun., 2016, DOI: 10.1039/c6md00006a.


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